Abstract
A selective, practical, and large-scale synthesis of [6]cycloparaphenylene, the second smallest cycloparaphenylene to be synthesized, was achieved in nine steps starting from commercially available 1,4-dibromobenzene and 4′-bromobiphenyl-4-ol. The key intermediate, <i>cis</i>-1,4-(4-bromophenyl)-1,4-bis(triethylsiloxy)cyclohexa-2,5-diene, was prepared on a large scale (>20 g) and was selectively dimerized to form a cyclic precursor of [6]cycloparaphenylene by platinum-mediated assembly and subsequent reductive elimination. Deprotection of the triethylsilyl group and subsequent tetrachlorostannic acid (H<sub>2</sub>SnCl<sub>4</sub>)-mediated reductive aromatization gave [6]cycloparaphenylene in 23% overall yield from the commercially available substrates on gram scale.
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